A large lake surrounded by residential areas, a park with a playground, and a road with parked cars.

Wakefield Holiday Rentals

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Our top choices for Wakefield holiday rentals

1. Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
Wakefield
9.6 out of 10, Exceptional, (9 reviews)
"Great stay"
United States
Alex c.
The price is NZ$953
includes taxes & fees
30 Sept - 1 Oct
Stylish home next to train to Boston, near Salem

2. Beautiful condo next to commuter rail into Boston

Beautiful condo next to commuter rail into Boston
Wakefield
9.6 out of 10, Exceptional, (29 reviews)
"The home was in a great neighborhood. The home is also super clean and hosts were responsive and helpful. "
United States
Melissa A.
The price is NZ$1,084
includes taxes & fees
28 Sept - 29 Sept
Beautiful condo next to commuter rail into Boston

3. Spacious 7-Room House Near Boston & Salem With Yard and Parking

Spacious 7-Room House Near Boston & Salem With Yard and Parking
Wakefield
10.0 out of 10, Exceptional, (18 reviews)
"Loved everything about this property! Hosts were very accommodating and communicated quickly and effectively. The home is very comfortable and spacious. Everything was clean and in good working condition. For those that aren’t familiar with Wakefield, it’s a charming town with many shops, restaurants and the centerpiece that is the lake. Highly reccomend!"
United States
Christopher C.
The price is NZ$1,344
includes taxes & fees
13 Oct - 14 Oct
Spacious 7-Room House Near Boston & Salem With Yard and Parking

4. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
The price is NZ$461
includes taxes & fees
28 Sept - 29 Sept
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

5. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Melrose
10.0 out of 10, Exceptional, (152 reviews)
"We enjoyed our stay! The house is beautiful, clean and as described. Greg was extremely helpful and very quick to respond. Neighborhood felt safe and would definitely stay again!"
United States
KATIE G.
The price is NZ$973
includes taxes & fees
29 Sept - 30 Sept
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

6. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (25 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is NZ$466
includes taxes & fees
21 Oct - 22 Oct
Enjoyable 2-bedroom lower level apartment in charming Lynn

7. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (328 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is NZ$555
includes taxes & fees
30 Sept - 1 Oct
Near Boston Historic two-bedroom with Modern Amenities

8. Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston

Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston
Beverly
10.0 out of 10, Exceptional, (6 reviews)
"Great little spot if you need to stay close to downtown Salem. Would recommend!"
United States
Corey W.
The price is NZ$882
includes taxes & fees
26 Oct - 27 Oct
Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston

9. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is NZ$570
includes taxes & fees
28 Sept - 29 Sept
Bright 2BR by Boston Waterfront

10. Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Ward Two
10.0 out of 10, Exceptional, (25 reviews)
"Can’t thank enough to Jorge and Eduardo for being such great hosts. The apartment is super cozy and close to everything. Quiet neighborhood, good and stores nearby. My kids loved it. About a 9minutes walk to Porter Sqr you can get easily to downtown Boston and its famous Freedom Trail. Supermarkets is about 7 minutes walking. Will definitely book this property again."
United States
Osvaldo
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

11. 3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
East Somerville
10.0 out of 10, Exceptional, (29 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is NZ$811
includes taxes & fees
4 Oct - 5 Oct
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

12. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is NZ$383
includes taxes & fees
25 Oct - 26 Oct
NEW Modern Apartment Near Boston & Harvard Square.

13. 3 bedroom apartment next to T stop / off street parking

3 bedroom apartment next to T stop / off street parking
Charlestown
9.8 out of 10, Exceptional, (70 reviews)
"Excellent location. Host was very responsive. Easy check in. Property was clean and as advertised. Highly recommend."
United States
Teresa M.
The price is NZ$585
includes taxes & fees
19 Oct - 20 Oct
3 bedroom apartment next to T stop / off street parking

14. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (481 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is NZ$376
includes taxes & fees
28 Sept - 29 Sept
Temple Place Suites

15. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"A little issue getting in with the door code operation but otherwise great"
United States
Unspecified U.
The price is NZ$458
includes taxes & fees
4 Oct - 5 Oct
Sleek Studio Apartment in the South End

16. Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
10.0 out of 10, Exceptional, (25 reviews)
"Great location Lots of walking to good food and a few great vintage and thrift stores"
United States
Christine L.
Re-listed: Adorable Condo Beverly - Salem - Halloween

17. The heart Cambridge/Boston Studio private yard free permit parking 1#

The heart Cambridge/Boston Studio private yard free permit parking 1#
Cambridgeport
9.4 out of 10, Exceptional, (93 reviews)
"Clean, comfy, cozy."
United States
Karen B.
The heart Cambridge/Boston Studio private yard free permit parking 1#

18. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (113 reviews)
"Rustic boathouse in a great central location ."
United States
William M.
The price is NZ$989
includes taxes & fees
13 Oct - 14 Oct
Fun houseboat. Walk to Boston attractions WIFI

19. Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marblehead
10.0 out of 10, Exceptional, (39 reviews)
"Adorable studio, has everything you could need! The host was super responsive and welcoming. Would absolutely stay there again. "
United States
Alisha J.
The price is NZ$549
includes taxes & fees
29 Sept - 30 Sept
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wakefield Hotel Reviews

Find out more about Wakefield

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wakefield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wakefield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wakefield. Seeing all the best attractions is bound to make you fall in love with Wakefield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wakefield short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Wakefield?

Yes, there are holiday rentals close to the most popular sights in Wakefield, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Wakefield speak positively about the scenic lakeside and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best holiday rentals that Wakefield has to offer?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Wakefield offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals are there in Wakefield?

Expedia has 5 holiday rentals for your stay in Wakefield.

What can I see and do in Wakefield?

Wakefield Dog Park and Breakheart Reservation are a couple of lovely local spots to get outside and enjoy nature. Fenway Park and Encore Boston Harbor are other popular places to visit in the area.

What are holiday rentals like in Wakefield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wakefield. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.